Will you support the rebels who want to leave the grip of the Empire or will you support the EMpire itself instead? Maybe you'll try to play both sides against each other for personal gain, or maybe you'll stay out of the conflict as much as possible.
So assuming you have a general idea of how your first character will behave, which side are you on?
Normally, I'd be expoliting the war for all it's worth, but on ym first character, a Dunmer patriot and seasoned Mercenary, I'll be supporting the rebels. The Empire's age is over, let it end already and let the people of Tamriel forge a new destiny for themselves. Besides, more conflict means more mercenary work for me.
EDIT: Added a poll, the second question isn't really essential, just something to answer if you feel like endulging me.
To make things a bit more manageable I decided that your first playthrough should apply, thus picking all the options is not possible, even if you intend to play hundreds of times in a row.